Activating SMTP AUTH (PLAIN) through STARTTLS in sendmail (FreeBSD)

N.B. This expects a working sendmail installation with STARTTLS Install cyrus-sasl # install cyrus-sasl2 cd /usr/ports/security/cyrus-sasl2 make install clean echo "pwcheck_method: saslauthd" > /usr/local/lib/sasl2/Sendmail.conf # install cyrus-sasl2-saslauthd cd /usr/ports/security/cyrus-sasl2-saslauthd make install clean echo 'saslauthd_enable="YES"' >> /etc/rc.conf service saslauthd start Set sendmail make flags Set the following flags in /etc/make.conf (create if it doesn’t exist) SENDMAIL_CFLAGS=-I/usr/local/include/sasl -DSASL SENDMAIL_LDFLAGS=-L/usr/local/lib SENDMAIL_LDADD=-lsasl2 Recompile sendmail Did you have the source in /usr/src? Otherwise you will need to run the following command....

Sendmail / Postfix - Testing mailserver

Links qmail.jms1.net BSD Handbook Sendmail.org This expects you to have netcat, perl and openssl installed Hello without TLS nc mail.server.com 25 220 mail.server.com ESMTP Sendmail 8.14.7/8.14.7; Thu, 11 Sep 2014 12:01:22 +0200 (CEST) > ehlo friendly.server.com 250-mail.server.com Hello friendly [1.2.3.4], pleased to meet you 250-ENHANCEDSTATUSCODES 250-PIPELINING 250-8BITMIME 250-SIZE 250-DSN 250-ETRN 250-AUTH DIGEST-MD5 CRAM-MD5 250-STARTTLS 250-DELIVERBY 250 HELP > quit< 221 2.0.0 mail.server.com closing connection Hello with TLS openssl s_client -starttls smtp -crlf -connect mail....